Last post, I promise:
http://dictionary.cambridge.org/dictionary/english/be-up-there-with-sb
"Up there with" clearly means equal to.
Therefore, if x is above y, x is not "up there with" y.
Therefore, "Messi doesn't deserve to be up there with Pele and Maradona" can, strictly speaking, be read as "Messi is above them"., even if that clearly isn't the implication of the sentence. It's therefore acceptable to twist the sentence this way for comic effect.

It's obvious we're going round in circles here, but you're flatly wrong. "Up there with" means "roughly on the same level as". Vynal was inverting the implications of last part of your post, while retaining the literal meaning, by saying that Messi isn't "up there with" those mentioned because he's above them. Hence paraprosdokian.
I don't know to make that any clearer, and obviously this isn't the place for this discussion. So there you go.

It absolutely is. Look up paraprosdokian. You know the Groucho Marx line "Outside of a dog, a book is a man's best friend. Inside of a dog it's too dark to read"? What you posted is the equivalent of saying "Actually Groucho, the first sentence implies that you're using "outside of" in an idiomatic sense to mean "apart from", meaning the second makes no sense"

I am, and the relevant word is "deserve". Something can "not deserve" to be grouped with something else either by being not good enough, or too good. "Messi doesn't deserve to be up there with Pele etc" is a strange way of saying he's better than them, but it's not exactly incorrect.
Of course it's contextually obvious what you mean, but, given Vynal Seven was jokingly decontextaulising it, that's irrelevant. That kind of joke relies on reading the sentence in a way which is unnatural, but technically valid. Obviously nobody thinks that's what you were actually saying.

That ranking system seems pretty flawed, since a South American team will only play a European team very rarely, so it's not really enough to judge the standard of league on. Also, if they are basing it on wins in the respective continental competitions, then they would have to assume a certain value for each of the competitions before they could compare the leagues.

It should technically be octopodes, but octopuses is the most commonly used one.
Anyway, so far I've got every prediction about this world cup right, although admittedly I've only made five, so I'm torn between predicting a Spain win, and quitting while I'm ahead.